Imagine having one of baseball’s brightest young stars in your organization—not once, but twice. That’s the enviable position the Pittsburgh Pirates have found themselves in, first with Paul Skenes and now with Konnor Griffin. But here’s where it gets controversial: while the Pirates let Skenes slip through their fingers, they now face a high-stakes decision with Griffin that could redefine their future—or haunt them for years. Did they learn from their past mistakes, or are they doomed to repeat them?**
The Pirates’ handling of Skenes is a cautionary tale. By the time extension talks surfaced, his value had already skyrocketed beyond what owner Bob Nutting was willing to invest. Griffin, however, presents a different scenario: a high-risk, high-reward opportunity that could pay dividends if executed correctly. The Pirates aren’t new to extensions—they’ve locked down Mitch Keller, Bryan Reynolds, and Ke’Bryan Hayes early in their careers. But those deals were cut during an era of team-friendly contracts, a trend that’s fading fast in today’s MLB. And this is the part most people miss: in a league where short-term megadeals are the norm, offering Griffin a long-term extension would be a bold, almost countercultural move.
Yet, there’s a blueprint for success. The Red Sox, for instance, have built a young core with long-term deals, like Ceddanne Rafaela’s eight-year, $50 million contract—signed just 49 days into his MLB career. While Rafaela isn’t as polished as Griffin is rumored to be, his deal shows that teams are still willing to bet big on potential. Could the Pirates follow suit? Dan Zangrilli of 93.7 The Fan hinted that a Griffin extension might have been on the table this winter, especially since Griffin shares an agency with Kyle Schwarber, whose rumored nine-figure deal could’ve opened the door for Griffin’s own massive contract.
Of course, there are risks. The Red Sox paid Kristian Campbell $2 million to spend most of last season in Triple-A, and the Pirates narrowly avoided a similar fate with Hayes, whose $7 million salary would’ve been a tough pill to swallow for his underwhelming bat. But as the Pirates’ window of contention opens, now is the time to roll the dice. Griffin’s talent is undeniable, and his extension could be the cornerstone of their future—or a costly misstep. What do you think? Is Griffin worth the gamble, or are the Pirates setting themselves up for another Skenes-sized regret? Let’s debate in the comments!
